[2] He began his career with Premier League side Manchester United in 1995 but was released two years later after failing to make a first-team appearance.

He joined Preston North End for £250,000 and managed to notch up 63 goals in 189 league matches until his departure to Manchester City in 2002.

[3] Following this success, Macken moved to fellow Division One side Manchester City in February 2002, for a fee of £5 million[3] and was part of the team that ended the season winning promotion to the Premier League.

This downturn in his career brought about a move away from Manchester and Macken joined Crystal Palace in the summer of 2005 for £1.1 million.

His own replacement, Dougie Freedman showed good form, and despite a recovery from injury, Macken did not get back in the team.

On deadline-day of the Summer 2006 transfer window, he made a further move to Ipswich Town in The Championship, this time on loan, being handed the number 27 shirt.

Derby were promoted to the Premier League at the end of the 2006–07 season, but he failed to win a regular place, or even score for The Rams, and was loaned out to Championship side Barnsley for two months in November 2007.

Although he was recalled on 27 December 2007[7] he eventually signed a permanent deal with the Tykes on 28 January 2008 for an undisclosed six-figure fee.

[11] On 31 January 2013, it was announced by Stockport County that Jon Macken had signed until the end of the 2012–13 season on a free transfer.

[12] Macken made his Stockport debut as a second-half substitute in County's 3–2 home win over Nuneaton Town on 2 February.

[14] Macken made his debut for the England U20 national team in June 1997; he replaced Danny Murphy in the 64th minute of the win against the United Arab Emirates during the 1997 FIFA World Youth Championship in Malaysia.

[18] On 18 August 2004, he made his debut when he replaced Clinton Morrison in the 63rd minute of the 1−1 draw with Bulgaria at Lansdowne Road.

[23] On 21 October 2024, Macken was appointed manager of Northern Premier League West Division side Stalybridge Celtic.